Synthesis and antimicrobial properties of substituted 3-aminoxypropionyl and 3-aminoxy-(E)-2-methoxyiminopropionyl monobactams.
The substituted 3-aminoxyproprionyl (VII) and 3-aminoxy-(E)-2-methoxyiminopropionyl monobactams (VIII) which possess the monocyclic beta-lactam nucleus of aztreonam (IX) were synthesized by reaction of triethylammonium (3S, 4S)-3-amino-4-methyl-2-oxo-1-azetidinsulfonate with the aminoxy acids X and XI, respectively. Compounds VII and VIII were assayed in vitro for their antimicrobial properties against Gram-positive and Gram-negative bacteria, whether producers of beta-lactamases or otherwise. Both types of compounds (VII and VIII) exhibited a poor antibacterial activity towards Gram-positive bacteria, comparable to that of aztreonam. On the contrary VII and VIII proved to be practically inactive against Gram-negative microorganisms, towards which aztreonam exhibits a high degree of activity.
Balsamo
A
A
Istituto di Chimica Farmaceutica e Tossicologica, Università di Pisa, Italy.
Macchia
B
B
Orlandini
E
E
Rossello
A
A
Macchia
F
F
Broccali
G
G
Fonio
W
W
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D001398:Aztreonam / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D005612:Freeze Drying; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008997:Monobactams / Q000138:chemical synthesis* / Q000494:pharmacology; D013055:Spectrophotometry, Infrared
D000900:Anti-Bacterial Agents; D008997:Monobactams; D001398:Aztreonam